Benzyl Bromide → Benzyl 5-hydroxypentanoate

Participants

Reaction Conditions

Reaction Steps

To a suspension of 569 mg (4.06 mmol) of sodium 5-hydroxypentanoate 69 in 3 mL of acetone was added 1.39 g (0.97 mL, 8.11 mmol, 2.0 equiv) of benzyl bromide and 65 mg (0.203 mmol, 0.05 equiv) of tetrabutylammonium bromide. The mixture was heated at 45° C. for 24 hours, cooled, and concentrated. The residue was dissolved in 200 mL of ethyl acetate, washed with 50 mL portions of 1N aqueous sodium bisulfate, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give 1.49 g of a pale yellow oil. Purification by MPLC (Lobar C-column, 45% ethyl acetate/hexane) have 641 mg (76%) of the title compound as an oil: 1H NMR (300 MHz, CDCl3) δ7.38-7.26 (m, 5H), 5.12 (s, 2H), 3.64 (t, 2H, J=6.3 Hz), 2.41 (t, 2H, J=7.2 Hz), 1.80-1.71 (m, 2H), 1.64-1.54 (m, 3H).

Provenance & Evidence